71159-90-5

Basic information

• Product Name: p-Menthene-8-thiol
• Synonyms: GRAPEFRUIT MERCAPTAN;FEMA 3700;ALPHA, ALPHA,4-TRIMETHYL-3-CYCLOHEXENE-1-METHANETHIOL;P-MENTHENE-8-THIOL;P-1-MENTHEN-8-THIOL;.alpha.,.alpha.-4-Trimethylcyclohex-3-ene-1-methanethiol;1-p-menthene-8-thiol;alpha,alpha,4-trimethyl-3-cyclohexene-1-methanethio
• CAS NO: 71159-90-5
• Molecular Formula: C₁₀H₁₈S
• Molecular Weight: 170.31
• EINECS: 275-223-1
• Product Categories: thiol Flavor
• Mol File: 71159-90-5.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 229.4 °C at 760 mmHg
• Flash Point: 90.7 °C
• Appearance: /
• Density: 0.938 g/cm³
• Vapor Pressure: 0.105mmHg at 25°C
• Refractive Index: 1.5
• PKA: 11.12±0.10(Predicted)
• CAS DataBase Reference: p-Menthene-8-thiol(CAS DataBase Reference)
• NIST Chemistry Reference: p-Menthene-8-thiol(71159-90-5)
• EPA Substance Registry System: p-Menthene-8-thiol(71159-90-5)

Safety Data

• Hazardous Substances Data: 71159-90-5(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 71159-90-5 differently. You can refer to the following data:
1. p-Menthene-8-thiol has been identified in grapefruit juice. It is a liquid with an extremely powerful, obnoxious odor; when diluted, it has the typical aroma of fresh grapefruit juice. Its odor threshold value is extremely low: 2×10-5 μg/kg for the (+)-R and 8×10-5 μg/kg for the (?)-S isomer.
2. 1-p-Menthene-8-thiol has an aroma and taste of grapefruit in dilute solution.

Occurrence

Reported found in grapefruit juice.

Aroma threshold values

Aroma characteristics at 0.01%: grapefruit, sulfurous catty, citrus, thiomenthone, slightly cooling, green rindy, juicy with nootkatone.

Taste threshold values

Taste characteristics at 0.01 ppm: bitter, waxy, citrus, clean grapefruit, fresh-squeezed juicy with nootkatone and orange juice nuances.

InChI:InChI=1/C10H18S/c1-8-4-6-9(7-5-8)10(2,3)11/h4,9,11H,5-7H2,1-3H3

Synthetic route

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether for 1h; Reduction;	90%

→ 2-(4-methylcyclohex-3-enyl)propane-2-thiol (71159-90-5)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether at 0 - 20℃; Solvent; Inert atmosphere;	85%

terpineol (98-55-5) → 2-(4-methylcyclohex-3-enyl)propane-2-thiol (71159-90-5)

Conditions	Yield
With Lawessons reagent In toluene for 0.5h; Heating;	20%
With tetraphosphorus decasulfide In tetrahydrofuran at 50℃; for 1h; Solvent; Reagent/catalyst; Temperature; Large scale;	500 g

(1R,5R)-(+)-β-pinene (127-91-3) → 2-(4-methylcyclohex-3-enyl)propane-2-thiol (71159-90-5) + trans-Pinane-2-thiol (88600-02-6) + 4-Methyl-2,4-di(4-methyl-3-cyclohexenyl)pentane-2-thiol (88600-04-8)

Conditions	Yield
With aluminum tri-bromide; hydrogen sulfide In chloroform at 20℃; for 0.5h; Yields of byproduct given;	A n/a B n/a C 13%
With aluminum tri-bromide; hydrogen sulfide In chloroform at 20℃; for 0.5h; Product distribution; EtAlClBr as reagent.;

(-)-α-pinene (7785-26-4) → 2-(4-methylcyclohex-3-enyl)propane-2-thiol (71159-90-5) + trans-Pinane-2-thiol (88600-02-6) + 4-Methyl-2,4-di(4-methyl-3-cyclohexenyl)pentane-2-thiol (88600-04-8)

Conditions	Yield
With aluminum tri-bromide; hydrogen sulfide In chloroform at 20℃; for 0.5h; Product distribution; EtAlClBr as reagent.;
With aluminum tri-bromide; hydrogen sulfide In chloroform

8,9-epthio-1-p-menthene (83108-08-1) → 2-(4-methylcyclohex-3-enyl)propane-2-thiol (71159-90-5)

Conditions	Yield
With lithium aluminium tetrahydride; 2-neopentoxyphenol; water 1.) THF, reflux, 1 h; 2.) 10 min; Yield given. Multistep reaction;

2-(4-methylcyclohex-3-enyl)propane-2-thiol (71159-90-5) → 1,8-epithio-p-menthane

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 70℃; for 1h;	97%

2-(4-methylcyclohex-3-enyl)propane-2-thiol (71159-90-5) → 2,8-epithio-cis-p-menthene

Conditions	Yield
With azobisisobutyronitrile In hexane at 70℃; for 2h;	65%

Upstream product

• 133490-04-7 α-terpinyl thiocyanate 
• 7783-06-4 hydrogen sulfide 
• 138-86-3 limonene. 
• 5989-27-5 D-limonene 
• 39864-10-3 α-terpinyl chloride 
• 83108-08-1 8,9-epthio-1-p-menthene 
• 127-91-3 (1R,5R)-(+)-β-pinene 
• 98-55-5 terpineol 
• 7785-26-4 (-)-α-pinene 
• 586-62-9 Terpinolene 

Relevant articles and documents

Method for preparing 1-poxlene -8-thiol

The invention belongs to the technical field of fine chemistry, and provides a method for preparing 1-poxlene-8-thiol, wherein a-terpineol is used as a raw material, and the a-terpineol reacts with athioreagent to obtain the 1-poxlene -8-thiol, the method comprises the following steps: dissolving the a-terpineol in an organic solvent; adding the thioreagent in batches to carry out a thioreaction;the system after reaction is cooled to room temperature, the solvent is removed through rotating evaporation, and sodium hydroxide aqueous solution is slowly added until the pH value is more than orequal to 12; extracting the water phase with methyl tert-ether twice, combining the organic phase, washing with saturated brine once, drying with anhydrous sodium sulfate, concentrating, and distilling under reduced pressure to obtain the product 1-poxlene-8-thiol. The method solves the problems that in the prior art, the synthesis route of the 1-poxlene-8-thiol is complex, the lithium aluminum tetrahydrate in the raw material is expensive, the danger is high, and the prior method is not suitable for industrial production.

ADDITION OF H2S TO TERPENES FOR PRODUCING NOVEL MOLAR MASS REGULATORS FOR RADICAL POLYMERISATIONS

The present invention relates to a method for producing thiols through addition of hydrogen sulfide onto at least one unsaturated terpene, where the reaction is carried out in the presence of at least one organic ion exchanger, and to the use of thiols derived from terpinolene as molar mass regulator in the polymerization of monomers.

Direct Conversion of Alcohols into Thiols

A simple one-pot reaction between alcohols and 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (Lawesson's reagent, LR) affords the corresponding thiols, accompanied by dehydration products, alkenes.Treatment of acyclic 1,4-diols with LR gives the 1,3-dienes. o-(Dihydroxymethyl)benzene derivatives yield the 1,3-dihydrobenzothiophenes when treated with LR.